Piperdine derivatives and hypotensives containing the same

ABSTRACT

A piperidine compound of the formula (I):                    
     wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH 2 ) n , which may be substituted, in which n is 0 or an integer of 1 to 10, —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N(COCH 3 )—, —N(COOC 2 H 5 )—, —N(CHO)—, —N(CH 3 )—, —CO—, —SO—, or —SO 2 —; Y is —CH≡CH—, —CH 2 CH 2 —, —CH 2 CO—, —O—, —S—, —NH—, —OCH 2 —, —SCH 2 —, —NHCH 2 —, —CH(OH)CH 2 — or —CH(OH)CH(OH)—; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the —(CH 2 )-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N(COCH 3 ), —N(COC 2 H 5 )—, —N(CHO)—, —N(CH 3 ), —CO—, —SO— or —SO 2 —, and wherein one or more of the —(CH 2 )-groups in X and Q may be substituted by —(CH 2 ) 4 — or —(CH 2 ) 5 — thereby forming a ring structure.

This application is a reissue application of application Ser. No.08/269,628, filed Jul. 1, 1994, now U.S. Pat. No. 5,393,890 which inturn is a continuation of application Ser. No. 08/072,458, filed Jun. 7,1993, now abandoned, which is a continuation of application Ser. No.07/655,775, filed Feb. 15, 1991, now U.S. Pat. No. 5,250,681, which is acontinuation of application Ser. No. 07/443,438, filed Nov. 30, 1989,now abandoned, which is a continuation of application Ser. No.07/354,880, filed May 22, 1989, now U.S. Pat. No. 5,231,105, which is acontinuation of application Ser. No. 07/201,911, filed Jun. 2, 1988, nowabandoned.

BACKGROUND OF THE INVENTION FIELD OF THE INVENTION

The present invention relates to a piperidine derivative andhypotensives containing the same.

DESCRIPTION OF THE BACKGROUND

It is said that there are about 13,000,000 patients with hypertension inJapan and its frequency of occurrence in individuals becomes greaterwith advancing age. Further, as the age of a given population increases,increased attention is directed to hypertension which becomes more andmore of a dangerous factor in severe heart and cerebral diseasesrepresented by cardiac infarction and cerebral apoplexy. In recentyears, calcium antagonists or angiotensin convertase inhibitors havebeen widely used as excellent primary selection drugs for treatment ofhypertension. But the pharmaceutical effects or safety of thesehypotensives have recently come into question.

A need therefore continues to exist for new hypotensive agents whichexhibit excellent pharmaceutical effects and safety which can beindustrially prepared at low cost and in a simple manner.

SUMMARY OF THE INVENTION

Accordingly, one object of the present invention is to provide aneffective hypotensive agent which is relatively simple to prepare at lowcost.

Briefly, this object and other objects of the present invention ashereinafter will become more readily apparent can be attained by apiperidine derivative of formula (I):

wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; Xis (CH₂)_(n), which may be substituted, in which n is 0 or an integer of1 to 10, —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N(COCH₃)—, —N(COOC₂H₅)—,—N(CHO)—, —N(CH₃)—, —CO—, —SO—, or —SO₂—; Y is —CH≡CH—, —CH₂CH₂—,—CH₂CO—, —O—, —S—, —NH—, —OCH₂—, —SCH₂—, —NHCH₂—, —CH(OH)CH₂—or —CH (OH)CH (OH) —; and Q is substituted or unsubstituted n-hexyl, carboxypropyl,ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl,naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl,tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl,oxazolyl or N-methylpyrolyl, wherein any one or more of the—(CH₂)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl andcyanopropyl groups may be replaced by —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N(COCH₃), —N(COC₂H₅)—, —N(CHO)—, —N(CH₃)—, —CO—, —SO— or —SO₂—, andwherein one or more of the —(CH₂)-groups in X and Q may be substitutedby —(CH₂)₄— or —(CH₂)₅— thereby forming a ring structure.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

It has now been discovered that piperidine derivatives of the formula(I) above are effective as hypotensive agents. The present piperidinederivative exhibits excellent hypotensive action, its method ofsynthesis is simple and its derivatives can be easily prepared.

In formula (I), the fused aromatic ring (A) is a fused benzene,thiophene, pyridine or the like ring. Further, in formula (I) above,substituents X and Q may be substituted by at least one substituentselected from the group consisting of H(CH2)n, wherein n is 1 to 10,C₁(CH₂)₃, allyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro,chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxy, carboxyl,methoxycarbonyl, ethoxycarbonyl, cyano, imidazolylmethyl,trifluoromethyl, benzoyl, 2-hydroxybenzyl, nitro, amino, acetylamino,propanoylamino, butanoylamino, pivaloylamino, trifluoromethylamino,methoxycarbonylamino, ethoxycarbonylamino, cinnamoylamino,methanesulfonylamino, N,N-bis(methanesulfonyl)amino, aminocarbonyl,aminosulfonyl, hydroxymethyl and acetoxymethyl.

The method of administration of the present piperidine derivative whenused as a hypotensive, include oral and parenteral routes. Dose isdetermined depending upon age, body weight and condition of the patientand route of administration. Daily dose is generally 0.01 to 2000 mg/kgfor oral administration. In the case of parenteral administration, thedaily dose is 0.01 to 1000 mg/kg. The present piperidine derivative maybe prepared in the form of ordinary preparations such as for example,tablets, powders, capsules, solutions, sugar—coated tablets or depots,which may be prepared in a conventional manner using conventionalpreparation aids. For example, tablets can be obtained by mixing thepiperidine derivative of the present invention diluents (e.g., lactose,calcium carbonate or calcium phosphate), binders (e.g., gum arabic, cornstarch or gelatin), swelling agents (e.g., alginic acid, corn starch orpregelinated starch), sweeteners (e.g., sucrose or saccharin), flavors(e.g., peppermint, Gaultheria adenothrix oil or cherry), lubricating andwetting agents (e.g., magnesium stearate, talc or carboxymethylcellulose).

Having now generally described this invention, a further understandingcan be obtained by reference to certain specific examples which areprovided herein for purposes of illustration only and are not intendedto be limited unless otherwise specified.

Unless otherwise indicated, the developing conditions for silica gel TLCprocedures were under chloroform/methanol−9/1. Mass spectra (MS) wereperformed in the FD mode (m/z) and nuclear magnetic resonance spectra(NMR) were measured using tetramethylsilane as the internal standard andCDCl₃ as the solvent.

EXAMPLE 1 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidinehydrochloride

A solution of 273 mg (1 mmol) of4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidine, 165 mg (1mmol) of 1-bromohexane, 745 mg (5 mmols) of sodium iodide and 414 mg (3mmols) of potassium carbonate in 20 ml of methyl isobutyl ketone wasstirred and refluxed at 120° C. overnight on an oil bath. After thereaction, the mixture was washed by adding 20 ml of water thereto. Thenthe organic phase was separated and the solvent was distilled off underreduced pressure. After purifying by silica gel column chromatography(eluent: methanol/chloroform, 1/100-1/50), the product was convertedinto the hydrochloride with an equimolar hydrogen chloride/dioxanesolution.

Amount yielded 180 mg

Yield 46%

TLC Rf=0.68

MS 357 (M+)

NMR 0.83 (3H, t), 1.2-1.4 (6H, m), 1.7-1.9 (2H, m), 2.31 (2H, dd), 2.53(2H, d), 2.7-2.8 (2H, m), 3.14 (2H, dd), 3.38 (2H, dd), 3.38 (2H, d),6.92 (2H, s), 7.2-7.4 (8H, m)

Hereafter procedures were carried out in manner similar to Example 1.

EXAMPLE 2 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-octylpiperidinehydrochloride

Amount yielded 300 mg

Yield 72%

TLC Rf=0.71

MS 385 (M+)

NMR 0.85 (3H, t), 1.2-1.4 (10H, m), 1.7-2.0 (2H, m), 2.30 (2H, dd), 2.53(2H, d), 2.7-2.9 (2H, m), 3.13 (2H, dd), 3.38 (2H, d), 6.90 (2H, s),7.1-7.4 (8H, m)

EXAMPLE 3 1-Decyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride

Amount yielded 300 mg

Yield 67%

TLC Rf=0.75

MS 413 (M+)

NMR 0.85 (3H, t), 1.2-1.4 (14H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.54(2H, d), 2.7-2.8 (2H, m), 3.15 (2H, dd), 3.39 (2H, d), 6.92 (2H, s),7.1-7.4 (8H, m)

EXAMPLE 4 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-dodecylpiperidinehydrochloride

Amount yielded 1.10 g

Yield 92%

TLC Rf=0.78

MS 441 (M+)

NMR 0.85 (3H, t), 1.1-1.5 (18H, m), 1.7-1.9 (2H, m), 2.32 (2H, dd), 2.54(2H, d), 2.7-2.8 (2H, m), 3.12 (2H, dd), 3.36 (2H, d), 6.93 (2H, s),7.1-7.4 (8H, m)

EXAMPLE 54-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-tetradecylpiperidinehydrochloride

Amount yielded 1.20 g

Yield 95%

TLC Rf=0.78

MS 469 (M+)

NMR 0.82 (3H, t), 1.1-1.5 (22H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.55(2H, d), 2.7-2.8 (2H, m), 3.15 (2H, dd), 3.40 (2H, d), 6.92 (2H, s),7.1-7.4 (8H, m)

EXAMPLE 6 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-hexadecylpiperidinehydrochloride

Amount yielded 1.18 g

Yield 88%

TLC Rf=0.80

MS 497 (M+)

NMR 0.80 (3H, t), 1.1-1.6 (26H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.58(2H, d), 2.7-2.8 (2H, m), 3.20 (2H, dd), 3.40 (.2H, d), 6.88 (2H, s),7.1-7.4 (8H, m)

EXAMPLE 71-Cyclohexylmethyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride

Amount yielded 520 mg

Yield 51%

TLC Rf=0.75

MS 369 (M+)

NMR 0.8-2.1 (11H, m), 2.42 (2H, dd), 2.65 (2H, d), 2.78 (2H, d), 3.20(2H, dd), 3.42 (2H, d), 6.91 (2H, s), 7.1-7.4 (8H, m)

EXAMPLE 81-Cyclohexyl-2-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethanehydrochloride

Amount yielded 780 mg

Yield 74%

TLC Rf=0.75

MS 383 (M+)

NMR 0.8-2.1 (13H, m), 2.45 (2H, dd), 2.67 (2H, d), 2.7-2.9 (2H, m), 3.0(2H, dd), 3.48 (2H, d), 6.94 (2H, s), 7.1-7.4 (8H, m)

EXAMPLE 91-Cyclohexyl-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride

Amount yielded 1.02 g

Yield 94%

TLC Rf=0.77

MS 397 (M+)

NMR 0.8-2.1 (15H, m), 2.47 (2H, dd), 2.68 (2H, d), 2.7-2.9 (2H, m), 3.0(2H, dd), 3.49 (2H, d), 6.94 (2H, s), 7.1-7.4 (8H, m)

EXAMPLE 101-Cyclohexyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanehydrochloride

Amount yielded 815 mg

Yield 72%

TLC Rf=0.78

MS 411 (M+)

NMR 0.8-2.1 (17H, m), 2.28 (2H, dd), 2.52 (2H, 2.7-2.9 (2H, m), 3.08(2H, dd), 3.35 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m)

EXAMPLE 111-Cyclohexyl-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)pentanehydrochloride

Amount yielded 750 mg

Yield 65%

TLC Rf=0.80

MS 411 (M+)

NMR 0.8-2.1 (19H, m), 2.25 (2H, dd), 2.68 (2H, d), 2.7-2.9 (2H, m), 3.12(2H, dd), 3.38 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m)

EXAMPLE 12 1-Benzyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride

Amount yielded 320 mg

Yield 80%

TLC Rf=0.42

MS 363 (M+)

NMR 2.28 (2H, dd), 2.52 (2H, d), 3.14 (2H, dd), 3.31 (2H, d), 4.01 (2H,d), 6.90 (2H, s), 7.1-7.6 (13H, m)

EXAMPLE 132-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylethanehydrochloride

Amount yielded 310 mg

Yield 75%

TLC Rf=0.45

MS 377 (M+)

NMR 2.28 (2H, dd), 2.51 (2H, d), 3.0-3.3 (6H, m), 3.47 (2H, d), 6.90(2H, s), 7.1-7.4 (13H, m)

EXAMPLE 143-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylpropanehydrochloride

Amount yielded 330 mg

Yield 77%

TLC Rf=0.50

MS 391 (M+)

NMR 2.1-2.4 (4H, m), 2.51 (2H, d), 2.65 (2H, t), 2.7-2.9 (2H, m), 3.12(2H, dd), 3.38 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 154-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylbutanehydrochloride

Amount yielded 180 mg

Yield 41%

TLC Rf=0.50

MS 405 (M+)

NMR 1.4-1.9 (4H, m), 2.28 (2H, dd), 2.52 (2H, d), 2.61 (2H, t), 2.7-2.8(2H, m), 3.12 (2H, .dd), 3.35 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 165-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylpentanehydrochloride

Amount yielded 110 mg

Yield 24%,

TLC Rf=0.55

MS 419 (M+)

NMR 1.2-1.9 (6H, m), 2.25 (2H, dd), 2.52 (2H, d), 2.60 (2H, t), 2.7-2.8(2H, m), 3.08 (2H, dd), 3.35 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 176-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylhexanehydrochloride

Amount yielded 315 mg

Yield 67%

TLC Rf=0.56

MS 433 (M+)

NMR 1.1-1.9 (8H, m), 2.26 (2H, dd), 2.56 (2H, d), 2.61 (2H, t), 2.7-2.8(2H, m), 3.10 (2H, dd), 3.35 (2H, d), 6.91 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 187-(4-(5H-Dibenzo[a,d]cyctohepten-5-ylidene)-1-piperidinyl)-1-phenylheptanehydrochloride

Amount yielded 267 mg

Yield 55%

TLC Rf=0.56

MS 447 (M+)

NMR 1.1-1 (10H, m), 2.25 (2H, dd), 2.55 (2H, d), 2.65 (2H, t), 2.7-2.8(2H, m), 3.07 (2H, dd), 3.32 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 192-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxyethanehydrochloride

Amount yielded 1.95 g

Yield 55%

TLC Rf=0.56

MS 393 (M+)

NMR (fee base) 2.1-2.5 (2H, m), 2.58 (2H, t), 2.6-2.7 (2H, m), 4.05 (2H,t), 6.89 (2H, d), 6.92 (2H, s), 7.1-7.4 (11H, m)

EXAMPLE 203-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxypropanehydrochloride

Amount yielded 2.15 g

Yield 48%

TLC Rf=0.58

MS 407 (M+)

NMR (free base) 1.97 (2H, tt), 2.1-2.5 (6H, m), 2.54 (2H, t), 2.6-2.7(2H, m), 3.97 (2H, dd), 6.86 (2H, d), 6.90 (2H, s), 7.1-7.4 (11H, m)

EXAMPLE 214-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxybutanehydrochloride

Amount yielded 1.18 g

Yield 86%

TLC Rf=0.61

MS 421 (M+)

NMR (free base) 1.8-2.7 (14H, m), 3.96 (2H, t), 6.87 (2H, d), 6.90 (2H,s), 7.1-7.4 (11H, m)

EXAMPLE 222-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthioethanehydrochloride

Amount yielded 0.97 g

Yield 87%

TLC Rf=0.55

MS 409 (M+)

NMR (free base) 2.0-2.6 (10H, m), 2.78 (2H, t), 6.86 (2H, s), 7.1-7.4(11H, m)

EXAMPLE 233-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthiopropanehydrochloride

Amount yielded 0.85 g

Yield 74%

TLC Rf=0.62

MS 423 (M+)

NMR (free base) 1.73 (2H, tt), 2.0-2.6 (10H, m), 2.80 (2H, t), 6.88 (2H,d), 7.1-7.4 (11H, m)

EXAMPLE 244-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthiobutanehydrochloride

Amount yielded 0.85 g

Yield 72%

TLC Rf=0.62

MS 437 (M+)

NMR (free base) 1.6-2.6 (14H, m), 2.80 (2H, t), 6.88 (2H, d), 7.1-7.4(11H, m)

EXAMPLE 254-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(2-nitrobenzenesulfonyl)aminoethyl)piperidine hydrochloride

TLC Rf=0.72

MS 502 (M+)

EXAMPLE 261-(2-(2-Aminobenzenesulfonyl)aminoethyl)-4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidinehydrochloride

TLC Rf=0.51

MS 472 (M+)

EXAMPLE 274-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(2-ethoxycarbonylbenzenesulfon6yl)aminoethyl)piperidinehydrochloride

TLC Rf=0.68

MS 544 (M+)

EXAMPLE 283-(2-((4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl)-2,4(1H,3H)quinazolinedionehydrochloride

TLC Rf=0.85

MS 462 (M+)

EXAMPLE 295,6-Benzo-2,4-diazo(2-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl)tetrahydrothiopyranehydrochloride

TLC Rf=0.91

MS 498 (M+)

EXAMPLE 302-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimethoxyphenyl)ethanehydrochloride

TLC Rf=0.78

MS 450 (M+)

EXAMPLE 315-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride

TLC Rf=0.92

MS 532 (M+)

NMR 0.77 (3H, d), 1.18 (3H, d), 1.6-3.3 (15H, m), 3.86 (3H, s), 3.92(3H, s), 6.8-7.4 (11H, m)

EXAMPLE 323-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propyl-4-fluorophenylsulfoxidehydrochloride

TLC Rf=0.78

MS 457 (M+)

EXAMPLE 333-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propyl-4-fluorophenylsulfonehydrochloride

TLC Rf=0.62

MS 473 (M+)

EXAMPLE 344-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(2-aminophenylthio)-1-propyl)piperidinehydrochloride

TLC Rf=0.84

MS 439 (M+)

EXAMPLE 354-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-(2-benzoylamino)ethyl)piperidinehydrochloride

TLC Rf=0.84

MS 420 (M+)

EXAMPLE 364-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-(2-N-phenylcarbamoylamino)ethyl)piperidinehydrochloride

TLC Rf=0.55

MS 435 (M+)

EXAMPLE 37

1-(3-(2-Cinnamoylaminophenylthio)-1-propyl)-4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidinehydrochloride

TLC Rf=0.66

MS 568 (M+)

NMR (free base) 1.74 (2H, tt), 2.0-2.6 (8H, m), 2.80 (2H, t), 6.59 (1H,d), 6.88 (2H, s), 7.0-7.6 (16H, m), 7.75 (1H, d), 8.5 (1H, d), 8.68 (1H,bs)

EXAMPLE 38 1-Cinnamyl-4- (5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride

TLC Rf=0.84

MS 389 (M+)

NMR (free base) 2.1-2.7 (8H, m), 3.15 (2H, d), 6.25 (1H, td), 6.47 (1H,d), 6.90 (2H, s), 7.1-7.4 (13H, m)

EXAMPLE 395-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4,5-trimethoxyphenyl)-2-isopropylvaleronitrilehydrochloride

TLC Rf=0.80

MS 563 (M+)

EXAMPLE 402-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-2-phenyl-1,3-dithiane-1,1,3,3-tetroxidehydrochloride

TLC Rf=0.48

MS 573 (M+)

EXAMPLE 412-(3,4-Dimethoxyphenyl)-2-(3-(4-(5H-dibenzo[a,d]cyclohepten-5ylidene)-1-piperidinyl)-1-propyl)-1,3-dithiane-1,1,3,3-tetroxidehydrochloride

TLC Rf=0.48

MS 573 (M+)

EXAMPLE 425-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dichlorophenyl)-2-isopropylvaleronitrilehydrochloride

TLC Rf=0.94

MS 540 (M+)

EXAMPLE 432-(3-Benzoylphenyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylvaleronitrilehydrochloride

TLC Rf=0.88

MS 548 (M+)

EXAMPLE 445-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2,2-diphenylvaleronitrilehydrochloride

TLC Rf=0.74

MS 506 (M+)

EXAMPLE 454-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3,4-dimethoxybutyrophenonehydrochloride

TLC Rf=0.61

MS 479 (M+)

EXAMPLE 466-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylhexanenitrilehydrochloride

TLC Rf=0.86

MS 430 (M+)

EXAMPLE 476-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylhexanenitrilehydrochloride

TLC Rf=0.88

MS 472 (M+)

EXAMPLE 486-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylhexanenitrilehydrochloride

TLC Rf=0.81

MS 546 (M+)

EXAMPLE 497-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylheptanenitrilehydrochloride

TLC Rf=0.84

MS 444 (M+)

EXAMPLE 507-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylheptanenitrilehydrochloride

TLC Rf=0.84

MS 486 (M+)

EXAMPLE 517-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylheptanenitrilehydrochloride

TLC Rf=0.86

MS 560 (M+)

EXAMPLE 522-(3-Chloropropyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrilehydrochloride

TLC Rf=0.92

MS 506 (M+)

EXAMPLE 535-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2--phenyl-2-phenylthiovaleronitrilehydrochloride

TLC Rf=0.81

MS 538 (M+)

EXAMPLE 545-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-phenylthiovaleronitrilehydrochloride

TLC Rf=0.91

MS 598 (M+)

EXAMPLE 555-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-naphthyl)valeronitrilehydrochloride

TLC Rf=0.85

MS 580 (M+)

EXAMPLE 565-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-naphthyl)-2-isopropylvaleronitrilehydrochloride

TLC Rf=0.90

MS 522 (M+)

EXAMPLE 575-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-naphthyl)valeronitrilehydrochloride

TLC Rf=0.85

MS 480 (M+)

EXAMPLE 585-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-naphthyl)-2-isopropylvaleronitrilehydrochloride

TLC Rf=0.87

MS 522 (M+)

EXAMPLE 595-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-trifluoromethylphenyl)valeronitrilehydrochloride

TLC Rf=0.72

MS 498 (M+)

EXAMPLE 605-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-trifluoromethylphenyl)valeronitrilehydrochloride

TLC Rf=0.75

MS 540 (M+)

EXAMPLE 618-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenyloctanenitrilehydrochloride

TLC Rf=0.84

MS 472 (M+)

EXAMPLE 628-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenyloctanenitrilehydrochloride

TLC Rf=0.88

MS 514 (M+)

EXAMPLE 638-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropyloctanenitrilehydrochloride

TLC Rf=0.82

MS 574 (M+)

EXAMPLE 641-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-1-indanenitrilehydrochloride

TLC Rf=0.90

MS 456 (M+)

EXAMPLE 651-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-5,6-dimethoxy-1-indanenitrilehydrochloride

TLC Rf=0.85

MS 516 (M+)

EXAMPLE 665-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-methylpyrrol-2-yl)valeronitrilehydrochloride

TLC Rf=0.61

MS 433 (M+)

EXAMPLE 675-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(1-methylpyrrol-2-yl)valeronitrilehydrochloride

TLC Rf=0.71

MS 475 (M+)

EXAMPLE 685-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(pyrrol-2-yl)valeronitrilehydrochloride

TLC Rf=0.55

MS 461 (M+)

EXAMPLE 695-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-α-hydroxybenzyl)phenyl)-2-methylvaleronitrilehydrochloride

TLC Rf=0.51

MS 550 (M+)

EXAMPLE 702-(3-Benzoylphenyl)-6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylhexanenitrilehydrochloride

TLC Rf=0.88

MS 562 (M+)

EXAMPLE 716-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-α-hydroxybenzyl)-phenyl-2-methylhexanenitrilehydrochloride

TLC Rf=0.52

MS 564 (M+)

EXAMPLE 722-(3-Benzoylphenyl)-7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylheptanenitrilehydrochloride

TLC Rf=0.91

MS 576 (M+)

EXAMPLE 737-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-(α-hydroxybenzyl)phenyl-2-methylheptanenitrilehydrochloride

TLC Rf=0.52

MS 578 (M+)

EXAMPLE 742-(3-Benzoylphenyl)-8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyloctanenitrilehydrochloride

TLC Rf=0.90

MS 590 (M+)

EXAMPLE 758-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-(α-hydroxybenzyl)phenyl-2-methyloctanenitrilehydrochloride

TLC Rf=0.61

MS 592 (M+)

EXAMPLE 765-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.91

MS 544 (M+)

EXAMPLE 775-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-methylvaleronitrilehydrochloride

TLC Rf=0.85

MS 504 (M+)

EXAMPLE 785-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.92

MS 458 (M+)

EXAMPLE 795-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-ethylvaleronitrilehydrochloride

TLC Rf=0.90

MS 518 (M+)

EXAMPLE 805-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-propyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.93

MS 472 (M+)

EXAMPLE 815-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-propylvaleronitrilehydrochloride

TLC Rf=0.91

MS 532 (M+)

EXAMPLE 822-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 486 (M+)

EXAMPLE 832-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)valeronitrilehydrochloride

TLC Rf=0.90

MS 546 (M+)

EXAMPLE 845-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-pentyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 500 (M+)

EXAMPLE 855-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-pentylvaleronitrilehydrochloride

TLC Rf=0.92

MS 560 (M+)

EXAMPLE 865-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 514 (M+)

EXAMPLE 875-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-hexylvaleronitrilehydrochloride

TLC Rf=0.92

MS 574 (M+)

EXAMPLE 885-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-heptyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 528 (M+)

EXAMPLE 895-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-heptylvaleronitrilehydrochloride

TLC Rf=0.91

MS 588 (M+)

EXAMPLE 905-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-octyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.94

MS 542 (M+)

EXAMPLE 915-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-octylvaleronitrilehydrochloride

TLC Rf=0.94

MS 602 (M+)

EXAMPLE 925-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-nonyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 556 (M+)

EXAMPLE 935-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-nonylvaleronitrilehydrochloride

TLC Rf=0.93

MS 616 (M+)

EXAMPLE 942-Decyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrilehydrochloride

TLC Rf=0.95

MS 570 (M+)

EXAMPLE 952-Decyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)valeronitrilehydrochloride

TLC Rf=0.94

MS 630 (M+)

EXAMPLE 965-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-acetophenonehydrochloride

TLC Rf=0.71

MS 391 (M+)

EXAMPLE 972-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylethanehydrochloride

TLC Rf=0.36

MS 393 (M+)

EXAMPLE 983-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propiophenonehydrochloride

TLC Rf=0.74

MS 405 (M+)

EXAMPLE 993-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylpropanehydrochloride

TLC Rf=0.35

MS 407 (M+)

EXAMPLE 1003-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyrophenonehydrochloride

TLC Rf=0.75

MS 419 (M+)

EXAMPLE 1014-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylbutanehydrochloride

TLC Rf=0.39

MS 421 (M+)

EXAMPLE 1025-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)valerophenonehydrochloride

TLC Rf=0.76

MS 433 (M+)

EXAMPLE 1035-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylpentanehydrochloride

TLC Rf=0.78

MS 447 (M+)

EXAMPLE 1042-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-fluoroacetophenonehydrochloride

TLC Rf=0.80

MS 409 (M+)

EXAMPLE 1052-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)ethanehydrochloride

TLC Rf=0.44

MS 411 (M+)

EXAMPLE 1063-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-fluoropropiophenonehydrochloride

TLC Rf=0.80

MS 423 (M+)

EXAMPLE 1073-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)propanehydrochloride

TLC Rf=0.44

MS 425 (M+)

EXAMPLE 1084-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)butanehydrochloride

TLC Rf=0.45

MS 439 (M+)

EXAMPLE 1095-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-fluorovalerophenonehydrochloride

TLC Rf=0.84

MS 451 (M+)

EXAMPLE 1105-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)pentanehydrochloride

TLC Rf=0.51

MS 453 (M+)

EXAMPLE 1114-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-fluorobenzyl)piperidinehydrochloride

TLC Rf=0.75

MS 381 (M+)

EXAMPLE 1124-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-fluorobenzyl)piperidinehydrochloride

TLC Rf=0.79

MS 381 (M+)

EXAMPLE 1134-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-fluorobenzyl)piperidinehydrochloride

TLC Rf=0.61

MS 381 (M+)

EXAMPLE 1144-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-trifluoromethylbenzyl)piperidinehydrochloride

TLC Rf=0.83

MS 431 (M+)

EXAMPLE 1154-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-trifluoromethylbenzyl)piperidinehydrochloride

TLC Rf=0.82

MS 431 (M+)

EXAMPLE 116 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinehydrochloride

TLC Rf=0.79

MS 431 (M+)

EXAMPLE 1174-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxybenzyl)piperidinehydrochloride

TLC Rf=0.61

MS 393 (M+)

EXAMPLE 1184-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxybenzyl)piperidinehydrochloride

TLC Rf=0.61

MS 393 (M+)

EXAMPLE 1194-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxybenzyl)piperidinehydrochloride

TLC Rf=0.52

MS 393 (M+)

EXAMPLE 1204-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-pentafluorobenzylpiperidinehydrochloride

TLC Rf=0.80

MS 453 (M+)

EXAMPLE 1215-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrilehydrochloride

TLC Rf=0.86

MS 440 (M+)

EXAMPLE 1225-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylvaleronitrilehydrochloride

TLC Rf=0.82

MS 488 (M+)

EXAMPLE 1235-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl-2-(3,4-dimethoxyphenyl)valeronitrilehydrochloride

TLC Rf=0.75

MS 500 (M+)

EXAMPLE 1242-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl-2-(4-fluorophenyl)-1,3-dioxolanehydrochloride

TLC Rf=0.68

MS 481 (M+)

EXAMPLE 1254-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-fluorobutyrophenonehydrochloride

TLC Rf=0.82

MS 437 (M+)

EXAMPLE 1265-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3,4,5-trimethoxyphenyl)valeronitrilehydrochloride

TLC Rf=0.66

MS 562 (M+)

MD TLC exp compound (M+) (Rf) solvent 1272-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl-1-(4-fluorophenyl)ethanehydrochloride 395 0.55 B 1281-(2-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 397 0.68 B 1291-(3-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 397 0.58 B 1301-(4-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 397 0.58 B 1314-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenyl)piperidinehydrochloride 377 0.74 B 1324-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methylbenyl)piperidinehydrochloride 377 0.71 B 1334-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methylbenyl)piperidinehydrochloride 377 0.65 B 1344-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-heptylpiperidinehydrochloride 371 0.70 B 1354-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-nondecylpiperidinehydrochloride 399 0.75 B 1364-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-undecylpiperidinehydrochloride 427 0.75 B 1374-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-tridecylpiperidinehydrochloride 455 0.78 B 1381-(2-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinedihydrochloride 392 0.38 B 1391-(3-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinedihydrochloride 392 0.23 B 1401-(4-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinedihydrochloride 392 0.26 B 1414-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrobenzyl)piperidinehydrochloride 422 0.85 B 1424-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrobenzyl)piperidinehydrochloride 422 0.82 B 1434-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrobenzyl)piperidinehydrochloride 422 0.83 B 1445-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-fluorophenyl)-2-isopropylvaleronitrile500 0.71 B hydrochloride 1455-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-methoxyphenyl)valeronitrile512 0.64 B hydrochloride 1465-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-methylphenyl)valeronitrile496 0.68 B hydrochloride 1475-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(2-549 0.78 B trifluoromethylphenyl)valeronitrile hydrochloride 1485-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(4-540 0.77 B trifluoromethylphenyl)valeronitrile hydrochloride 1495-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-(3-526 0.77 B trifluoromethylphenyl)valeronitrile hydrochloride 1502-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-554 0.80 B trifluoromethylphenyl)valeronitrile hydrochloride 1515-(4-(5H-Dibenzo[ac]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-(3-582 0.80 B trifluoromethylphenyl)valeronitrile hydrochloride 1524-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-phenyl-1-butenehydrochloride 403 0.51 B 1531-Benzyloxy-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethanehydrochloride 407 0.58 B 1541-Cyclohexyl-6-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)hexanehydrochloride 439 0.62 B 1551-Cyclohexyl-7-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)heptanehydrochloride 453 0.65 B 1561-Cyclohexyl-8-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)octanehydrochloride 467 0.68 B 1571-(4-Cyclohexylbutanoyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine425 0.75 B 1581-(2-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 388 0.83 B 1591-(3-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 388 0.85 B 1601-(4-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 388 0.70 B 1614-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-Picolyl)piperidinedihydrochloride 364 0.58 B 1624-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-Picolyl)piperidinedihydrochloride 364 0.53 B 1634-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-Picolyl)piperidinedihydrochloride 364 0.44 B 1641-Decanolyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine 427 0.75B 1651-Cyano-3-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 340 0.58 B 1661-Cyano-4-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 354 0.52 B 1672-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxyacetophenonehydrochloride 451 0.85 B 1683-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxypropiophenonehydrochloride 465 0.61 B 1695-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxyvalerophenonehydrochloride 193 0.64 B 1704-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′,5′-trimethoxybutyrophenone509 0.82 B hydrochloride 1714-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2′,3′,4′-trimethoxybutyrophenone509 0.86 B hydrochloride 1724-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-trimethoxybutyrophenone449 0.61 B hydrochloride 1734-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxybenzyl)piperidinehydrochloride 423 0.63 B 1744-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzyl)piperidinehydrochloride 423 0.73 B 1754-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzyl)piperidine437 0.58 B 1761-Cyclohexyl-3,(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propylketonehydrochloride 425 0.51 B 1772-Cyclohexyl-5,(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)valeronitrilehydrochloride 436 0.60 B 1781-(4-(3-Chloro-5H-dibenzo[a,d]cyclohepten-5-ylidene-1-piperidinyl)-4-cyclohexylbutanehydrochloride 445 0.62 B 1791-Cyclohexyl-(4-(3-methoxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanehydrochloride 441 0.59 B 1804,9-Dihydro-4-(1-(4-cyclohexylbutyl)-4-piperidinylidene-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one433 0.45 B hydrochloride 1811-(4-Cyclohexylbutyl-4-(9-xantylidene)piperidine hydrochloride 401 0.64B 182 1-(4-Cyclohexylbutyl-4-(9-thioxantylidene)piperidine hydrochloride417 0.65 B 1836,11-Dihydro-11-(1-(4-cyclohexylbutyl)-4-piperidinylidene-5H-dibenzop[5,6]cycloheptal[1,2-b]pyridine414 0.41 B dihydrochloride 1844-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxybenzyl)piperidinehydrochloride 395 0.73 B 1851-Decyl-4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 415 0.52 B 1861-Cyclohexyl-4-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptan-5-ylidene)-1-piperidinyl)butane413 0.67 B hydrochloride 1874-(4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxy-481 0.66 B butyrophenone hydrochloride 1884-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzyl)piperidine453 0.69 B 1894-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzoyl)piperidine467 0.71 B 1904-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenzoyl)piperidine391 0.73 B 1914-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(4-fluorophenyl)acetyl)piperidine409 0.76 B 1924-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-dimethoxycinnamoyl)piperidine463 0.73 B 1934-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-dimethoxycinnamyl)piperidinehydrochloride 449 0.46 B 1944-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-diethoxybutyrophenonehydrochloride 501 0.49 B 1951-(4-(4-Aminophenyl)butyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)piperidinedihydrochloride 420 0.34 B 1964-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(4-nitrophenyl)butyl)piperidinehydrochloride 450 0.50 B 1971-(4-(4-Acetylaminophenyl)butyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)piperidinedihydrochloride 462 0.48 B 1984-(4-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethylbutyrophenonehydrochloride 447 0.53 B 199 Ethyl4-(4-(5H-dibanzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyratehydrochloride 387 0.51 B 2004-((4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyric acid359 0.15 B 2014-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(-3-(3′,4′-dimethoxyphenyl)propyl)piperidinehydrochloride 451 0.60 B 2024-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(3′,4′-dimethoxyphenyl)propanoyl)piperidine465 0.78 B 2031-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)piperidinehydrochloride 426 0.60 B 204N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-1,2,3,4-tetrahydroisoquinoline474 0.42 B hydrochloride 2054-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimethoxy)phenyl-1-hydroxybutane481 0.38 B hydrochloride 2061-Acetoxy-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-(3,4-dimethoxy)phenylButane523 0.49 B hydroxybutane hydrochloride 2071-butyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimethoxy)phenyl-1-537 0.45 B hydroxybutane hydroxybutane hydrochloride 2081-(4-Methoxyxyxlohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane441 0.55 B hydroxybutane hydrochloride 2091-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)piperidine412 0.03 B dihydroxybutane hydrochloride 2104-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-N-imidazolylmethyl)cinnamyl)piperidine469 0.44 B dihydroxybutane hydrochloride 2114-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthoyl)piperidine 4270.88 B 2124-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthylmethyl)piperidinehydrochloride 413 0.94 B 2134-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthoyl)piperidine 4270.59 B 2144-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthylmethyl)piperidinehydrochloride 413 0.83 B 2152-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)cyclohexanonehydrochloride 426 0.50 B (H+ 2161-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-4-hydroxypiperidinehydrochloride 442 0.58 B 2171-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-4-ethoxyxarbonpiperidine499 0.26 B hydrochloride 218 Cyclohexyl3-(4-(5H-Dibenzo[a,d]cyclohpetan-5-ylidene)-1-piperidinyl)propyletherhydrochloride 413 0.48 B 2191-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-butyl)-1-methoxycarbonylcyclohexane470 0.55 B hydrochloride (H+) 220 Ethyl2-cyclohexyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)valeratehydrochloride 483 0.65 B 2214-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(3′,4′-dimethoxyphenyl)butyl)piperidinehydrochloride 465 0.66 B 2222-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl-2-(3,4-dimethoxyphenyl)-523 0.54 B 1,3-dioxolane hydrochloride 2231-Carboxyl-1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butylcyclohexanehydrochloride 456 0.38 B (H+) 2244-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphthoyl)piperidine431 0.90 B 2254-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphthylmethyl)piperidine417 0.55 B 226N-(3,(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanoyl)cyclohexylaminehydrochloride 426 0.64 B 2272-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylcyclohexanecarboxylate hydrochloride 427 0.71 B 2284-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-cyclohexylbutanehydrochloride 431 0.74 B 2294-(4-(5H-Dibenzo[a,d]thiepin-5-ylidene)-1-piperidinyl)-3+,4+-dimethoxybutyrophenonehydrochloride 499 0.46 B 2304-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidinehydrochloride 434 0.70 B 2311-(4-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 404 0.36 B 2321-(4-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidinedihydrochloride 446 0.27 B 2334-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-furyl)-1-butanonehydrochloride 409 B 2344-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-thienyl)-1-butanonehydrochloride 425 B 2353-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl(2-tetrahydropyranyl)ether415 0.55 B hydrochloride 236 Cyclohexyl3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propionatehydrochloride 427 0.71 B 237N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-4-nitrobenzamidehydrochloride 465 0.49 H 2382-Cyclohexyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyricacid 455 0.26 B 2393-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylphenylsulphoxide hydrochloride 409 0.29 H 2402-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl-5′,6′-dimethoxyindanhydrochloride 477 0.41 B 2413-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylphenylsulphone hydrochloride 441 0.36 B 242N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3′,4′-dimethoxybenzamidehydrochloride 480 0.44 G 243N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylcyclohexanecarboxamide hydrochloride 426 0.75 B 244N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicotinamide hydrochloride 421 0.20 B 2451-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)morpholinehydrochloride 428 0.31 C 2463-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)thiomorpholinehydrochloride 444 0.43 C 2473-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-notrophenyl)propanehydrochloride 436 0.34 H 2481-(4-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanedihydrochloride 406 0.13 B 2491-(4-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane448 0.43 B dihydrochloride 2503-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitrophenyl)propanehydrochloride 436 0.53 H 2511-(2-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanedihydrochloride 406 0.52 B 2521-(2-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane448 0.51 B dihydrochloride 2532-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylphenylsulphoxidehydrochloride 425 0.20 H 2542-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylphenylsulphone hydrochloride 455 0.71 B 2554-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitrophenyl)butanehydrochloride 450 0.49 H 256Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylsulphidehydrochloride 430 0.17 J (H+) 257Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylsulphoxidehydrochloride 445 0.51 B 258Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylsulphonehydrochloride 462 0.28 H (H+) 259 Ethyl2-cyclohexylmethyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyrate483 0.70 B hydrochloride 2601-(4-acetylamino-1-cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane468 0.43 B hydrochloride 2612-(2-4-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′,6′-dimethoxy-1-indanone477 0.41 B hydrochloride 262 Ethyl2-(2-cyclohexylethyl-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propionate483 0.74 B hydrochloride 263Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylsulfonehydrochloride 461 0.94 B 264Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylsulfoxide441 0.48 B hydrochloride (H+) 265Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylsulfidehydrochloride 429 0.85 B 2662-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4-amino-6,7-dimethoxyquinazoline476 0.34 B dihydrochloride 267N-Acetyl-N-(3-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylcyclohexylamine454 0.35 B hydrochloride 268N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-2-piperidonehydrochloride 426 0.39 B 2691-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-1-ethoxycarbonxylcyclohexane483 0.82 B hydrochloride 2703-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl)propanedihydrochloride 392 0.44 B 2714-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxybutyrophenoneN-oxide 477 0.45 B (M-18) 2721-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-1-hydroxymethylcyclohexane441 0.55 B hydrochloride 2731-Acetoxymethyl-1-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexane483 0.86 B hydrochloride 2744-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyl-3′,4′-dimethoxybutyrophenone493 0.22 B hydrochloride 2754-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-propyl)-3′,4′-dimethoxybutyrophenone521 0.28 H hydrochloride 2762-Allyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′dimethoxybutyrophenone519 0.30 H hydrochloride 2774-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-propyl)-3′,4′-dimethoxybutyrophenone521 0.38 H hydrochloride 2784-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-3′,4′-dimethoxybutyrophenone507 0.33 H hydrochloride 279Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl)etherhydrochloride 413 0.73 B 2801-(n-Acetyl-3-piperidinyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 440 0.75 B 2813-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-piperidinyl)propanedihydrochloride 398 0.16 A 2821-(3-Acetylamino-4-methoxyphenyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane492 0.58 B hydrochloride 2834-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexanehydrochloride 425 0.63 B 2843-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-pyridyl)-1-propanehydrochloride 390 0.66 H 2852,6-Dimethyl-4-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)-5-methyl-1,4-528 0.30 F dihydropyrydine-3,5-dicarboxylate hydrochloride 2863-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,3-dimethoxyphenyl)propanehydrochloride 451 0.68 H 2872-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5′,6′-dimethoxyindanhydrochloride 463 0.59 H 2882,6-Dimethyl-4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-5-methylpyrydine-527 0.68 B 3,5-dicarboxylate dihydrochloride 2893-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-pyridyl)propanedihydrochloride 392 0.37 B 290N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3-nitrobenzamidehydrochloride 466 0.48 D (H+) 291N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-2-nitrobenzamidehydrochloride 466 D (H+) 292N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-2,4-dimethoxybenzamidehydrochloride 481 0.31 D (H+) 2934-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-pyrolle)-1-butanehydrochloride 409 B (H+) 2941-(N-Acetyl-2-piperidinyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 440 0.30 B 2954-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(N-methyl-3-piperidinyl)butanedihydrochloride 426 0.07 B 2961-(1-(4-Hydroxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanehydrochloride 427 0.45 B 2971-(1-(4-Cyano)cyclohexyl)-4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanehydrochloride 436 0.55 F 2983-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-methoxyphenyl)propanehydrochloride 421 0.81 B 2991-(1-(3-Methoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane441 0.71 B hydrochloride 3001-(1-(3-Hydroxyoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane427 0.47 B hydrochloride 3013-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexanoehydrochloride 425 0.70 B 3024-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidinylhydrochloride 434 0.91 B 3031-(2-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinehydrochloride 404 0.62 B 3041-(2-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinehydrochloride 446 0.55 B 3054-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)tetrahydropyranhydrochloride 413 0.69 B 3064-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrocinnamyl)piperidinehydrochloride 984 0.90 B 3073-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-piperidinyl)propanedihydrochloride 398 0.07 A 3081-(N-acetyl-4-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 440 0.23 H 3093-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanedihydrochloride 398 0.03 B 3102-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indanehydrochloride 417 0.59 B 3114-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ehtyl)-2,4,5,6-tetramethyl-524 0.68 B 1,4-dihydropyridino-3,5-dicarboxylate hydrochloride 3124-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(N-ethoxycarbonyl-3-piperidinyl)butane484 0.64 B hydrochloride 3131-(5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-pentyl)-1-methoxycarbonylcyclohexane483 0.72 B hydrochloride 3141-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-1-methoxycarbonylcyclohexane455 0.75 B hydrochloride 3151-(3-Aminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanedihydrochloride 993 0.62 B 3161-(3-Acetylaminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanehydrochloride 994 0.48 B 3173-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4,5-trimethoxyphenyl)propane481 0.65 B dihydrochloride 3182-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5,6-dimethoxy-491 0.21 H 1,2,34-tetrahydronaphthalene hydrochloride 3196-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-2,3-dimethoxybenzocycloheptene491 0.56 H hydrochloride 3204-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxycinnamyl)piperdinehydrochloride 479 0.69 B 3211-(N-Acetyl-4-piperidinyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-pentene466 0.33 B dihydrochloride 3222-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-3,4,5,6-tetrmethyl-1000  0.30 B 1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 3232-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-3,4-5,6-tetramethylpyridine-550 0.43 B 3,5-dicarboxylate hydrochloride 3241-(1-(4-Methoxy)cyclohecyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane427 0.48 B hydrochloride 325(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrocinnamyl)piperidinehydrochloride 454 0.89 B 3261-(4-Aminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinedihydrochloride 424 0.65 B 3271-(4-Acetylaminominocinnamyl)-4-(5H-Dibenzo[a,d]thiepiz-5-ylidene)-1-piperidinehydrochloride 466 0.58 B 3283-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,4-dimethoxyphenyl)propanedihydrochloride 451 0.64 B 3292-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-4′-nitroindanhydrochloride 448 0.49 I 3304′-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindanhydrochloride 418 0.38 H 3314′Acetylamino-2(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-Piperidinyl)methylindanhydrochloride 460 0.33 B 3322-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5′-nitroindanhydrochloride 448 0.51 I 3335′-Amino2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindanhydrochloride 418 0.34 B 3345′-acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindanhydrochloride 460 0.29 H 3354-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylbenzamidehydrochloride 435 B 3363-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylbenzamidehydrochloride 435 B 3371-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonipecotinamidehydrochloride 455 B 3381-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicotinamidehydrochloride 455 B 339N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylnicotinamidehydrochloride 421 0.42 B 340N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethnicotinamideN-oxide hydrochloride 437 0.27 D (H+) 341N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicotinamideN-oxide hydrochloride 437 0.30 D (H+) 3424-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,4-dimethoxycinnamyl)piperidinehydrochloride 449 0.73 B 3434-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,5-dimethoxycinnamyl)piperidinehydrochloride 449 0.73 B 3444-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxycinnamyl)piperidinehydrochloride 449 0.90 B 3454-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,5-dimethoxycinnamyl)piperidinehydrochloride 449 0.74 B 3461-(4-Cyanocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinehydrochloride 414 0.70 B 3474-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycinnamyl)piperidinehydrochloride 419 0.87 B 3484-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycinnamyl)piperidinehydrochloride 419 0.89 B 3494-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 4190.85 B 3504-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrocinnamyl)piperidinehydrochloride 436 0.93 B 3511-(4-Aminocinnamyl)-4-(10,11-dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinedihydrochloride 406 0.64 B 352 1-(4-Acetylaminocinnamyl)-4-(10,11dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine 448 0.54 Bdihydrochloride 3534-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-4-fluorocinnamyl)piperidinehydrochloride 407 0.88 B 3542-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-4′-nitroindanhydrochloride 462 0.34 H 3554′-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indanhydrochloride 432 0.53 B 3564′-Caetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indanhydrochloride 474 0.24 B 3572-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′-nitroindanhydrochloride 462 0.31 H 3585′-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indandihydrochloride 432 0.23 H 3595′-Acetylamino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indandihydrochloride 474 0.05 H 3602-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′-methanesulfonylaminoindan510 0.11 H hydrochloride 3611-(Cyclohexyl-4-(4-(10,11-dihydroxy-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane445 0.84 B 3623-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl)-1-propenedihydrochloride 390 0.44 B 3634-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxycinnamyl)piperidinehydrochloride 406 0.55 B (H+) 3641-(4-Acetoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 447 0.87 B 3654-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxy-3-methoxycinnamyl)piperidinehydrochloridine 435 0.63 B 3661-(4-Acetoxy-3-methoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinehydrochloride 477 0.83 B 3674-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-hydroxycinnamyl)piperidinehydrochloride 405 0.45 B 3681-(3-Acetoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 447 0.80 B 3694-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(2-methoxyacetoxy)cinnamyl)piperidinehydrochloride 477 0.65 B 3704-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-propanoylaminocinnamyl)piperidinehydrochloride 460 0.21 H 3714-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarbonylaminocinnamyl)piperidinehydrochloride 476 0.20 H 3724-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methanesulfonylaminocinnamyl)piperidinehydrochloride 482 0.44 B 3731-(N,N-Bis(methanesulfonyl)amminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine560 0.88 B hydrochloride 3744-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycarbonylcinnamyl)piperidinehydrochloride 447 0.55 B 3754-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycarbonylcinnamyl)piperidinehydrochloride 447 0.48 H 3764-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylcinnamyl)piperidinehydrochloride 447 0.50 B 3774-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-3-methoxy-2-nitrocinnamyl)piperidinehydrochloride 464 0.30 H 3784-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylaminocinnamyl)piperidinehydrochloride 462 0.53 B 3794-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-pivaloy)aminocinnamyl)piperidinehydrochloride 488 0.51 B 3804-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-trifluoroacetylaminocinnamyl)piperidinehydrochloride 500 0.44 B 3811-(4-Butanoylaminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 474 0.50 B 3824-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarbonylcinnamyl)piperidinehydrochloride 477 0.85 B 3834-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(2-methoxyacetoxy)cinnamyl)piperidinehydrochloride 477 0.45 B 3844-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dihydroxycinnamyl)piperidinehydrochloride 422 0.35 B (H+) 3854-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-indolylmethyl)piperidinehydrochloride 402 0.67 H 3861-(4-Aminosulfonylcinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidinehydrochloride 468 0.48 B (H+) 3874-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxy-4-nitrocinnamyl)piperidinehydrochloride 464 0.29 H solvent: solvent for TLC A: chloroform/methanol= 4/1 B: chloroform/methanol = 9/1 C: chloroform/methanol = 20/1 D:chloroform/methanol = 25/1 E: chloroform/methanol = 50/1 F:ethylacetate/hexane = 5/1 G: ethylacetate/hexane = 3/1 H:ethylacetate/hexane = 1/1 I: ethylacetate/hexane = 1/2 G:ethylacetate/hexane = 1/5

EXAMPLE 154

As test animals, four male spontaneously hypertensive rats (weight 400to 440 g) that were sufficiently adapted for feeding and in whichhypertension was confirmed were used.

Physiological saline aqueous solution containing 2.5% Nicolle and 2.5%ethanol of sample was intravenously administered by bolus injection at adose of 1 ml per 1 kg of body weight. Systolic blood pressure afteradministration was measured by the indirect (tail-cuff) method.

The results are shown below.

Decrease in systolic blood pressure Dose (mmHg) time afteradministration (hour) Compound (mg/kg) 0.5 4 1 10 −67 1 2 10 −125 −34 33 −110 −22 4 10 −76 0 5 10 −56 −20 7 10 −57 −15 8 10 −95 −21 9 10 −91−19 10 10 −129 −21 11 10 −166 12 10 −27 1 13 10 −47 4 14 10 −105 −10 1510 −130 −136 16 10 −114 −30 17 10 −84 −16 20 10 −37 2 23 10 −34 10 25 10−8 −7 28 10 −52 4 31 10 −61 −11 37 10 −78 −36 38 10 −140 −76 42 10 −66−14 45 10 −147 −38 52 10 −23 −9 59 10 −87 −21 60 10 −121 −48 100 10 −35−5 101 10 −89 −14 107 10 −88 −11 108 10 −126 −50 111 10 −98 −13 112 10−16 0 113 1 −151 −81 115 10 −53 −19 116 10 −36 −12 117 10 −143 −25 11810 −129 −24 119 10 −34 −5 120 3 −17 −12 121 10 −42 −19 122 10 −120 −62123 10 −55 −7 124 10 −90 −20 125 10 −93 −14 126 10 −87 −19 128 10 −129−8 129 10 −17 −1 130 10 −42 9 131 10 −116 2 132 10 −106 −5 133 3 −146−84 134 10 −115 −30 135 10 −132 −50 136 10 −100 −40 138 10 −129 −33 13910 −139 −89 140 3 −113 −101 142 10 −43 0 149 10 −116 −32 150 10 −110 −47151 10 −81 −43 154 10 −131 −105 155 10 −131 −105 156 10 −110 −42 157 10−32 −13 158 10 −8 7 159 10 −27 −12 160 10 −3 −10 161 10 −64 −12 162 10−62 −3 163 10 −1 4 164 10 −91 −22 165 10 −22 12 166 10 −45 6 168 10 −1080 169 10 −130 −4 171 10 −122 −8 172 10 −115 −25 173 10 −98 −25 174 10 −8−16 175 10 −87 −1 176 10 −105 −10 180 10 −25 −24 181 10 −56 −27 182 10−11 −6 184 10 −16 −4 185 10 −66 −10 186 10 −95 −12 187 10 −47 −9 188 10−94 −12 189 10 −72 −15 190 10 −11 −15 191 10 −29 −20 192 10 −25 −36 19310 −124 −59 194 10 −59 −17 195 10 −100 −51 196 10 −145 −81 197 10 −51−26 198 10 −124 −25 199 10 −15 −24 200 10 −10 −24 201 10 −118 −21 202 10−54 −16 203 3 −123 −58 204 10 −141 −84 205 10 −22 −4 206 10 −61 −27 20710 −98 −43 208 10 −131 −19 209 10 −49 −13 210 1 −78 −69 212 10 −155 21310 −82 3 214 10 −126 −21 215 10 −128 −14 216 3 −2 −27 217 10 −18 −20 21810 −97 −11 219 10 −104 −33 220 10 −148 −54 221 10 −70 −13 222 10 −94 −5224 10 −69 −61 225 10 −115 −31 226 10 −131 −16 228 3 −112 −14 229 3 −77−14 230 3 −131 −91 231 3 −132 −115 232 1 −92 −85 233 10 −35 −1 234 10−96 −2 235 10 −99 −5 236 10 −10 −15 237 10 −65 −14 238 10 −14 −5 239 10−68 −15 240 3 −118 −5 241 10 −73 −4 242 10 −28 7 243 10 −111 −31 244 10−19 4 245 10 −34 −10 246 10 −34 −4 247 10 −119 −40 248 10 −101 −92 24910 −121 −100 250 10 −136 −30 251 10 −110 −24 252 10 −23 −5 253 10 −12 1255 10 −62 2 256 10 −60 −11 257 10 −70 −13 258 10 −74 −10 259 10 −46 −5260 10 −51 −10 261 10 −123 −11 262 10 −16 −3 264 10 −38 −5 265 10 −61−11 266 10 −133 −77 267 10 −40 0 268 10 −29 13 269 10 143 −71 270 10 −182 271 10 −17 −13 272 10 −76 −3 273 10 −37 5 274 10 −102 −21 275 10 −66−20 276 10 −24 −1 277 10 −27 0 278 10 −64 2 279 3 −83 −24 280 10 −50 −11281 10 −31 −5 282 10 −72 −15 283 10 −112 4 284 3 −151 −40 285 10 −62 −7286 10 −134 −40 287 10 −83 −16 288 10 −92 −14 289 3 −20 10 290 3 −15 15291 3 −8 15 292 3 −31 3 293 10 −122 4 294 3 −17 7 295 3 −36 1 296 10−109 −14 297 10 −129 −57 298 10 −111 −31 299 10 −134 −45 300 10 −97 −22301 10 −100 −12 302 10 −83 −41 303 3 −90 −19 304 10 −49 −5 305 10 −95 −9306 10 −138 −37 307 10 −62 −20 308 3 −27 −5 310 10 −90 −18 311 10 −90−18 312 10 −115 −11 313 10 −154 −85 314 10 −61 −11 315 10 −43 −3 316 1−100 8 317 10 −118 −14 318 10 −83 −57 319 10 −104 −20 320 10 −147 −113321 10 −60 −4 322 10 −100 −16 323 10 −117 −11 324 10 −137 −46 325 10−115 −100 326 1 −125 −102 327 3 −10 −43 328 10 −125 −87 329 10 −34 −7330 10 −93 −25 331 10 −62 −14 332 10 −111 −57 343 3 −83 −45 344 1 −123−35 345 3 −120 −95 346 3 −142 −121 347 3 −116 −53 348 3 −105 −12 349 1−48 −43 350 10 −136 −85 351 3 −70 −21 352 3 −93 −60 353 10 −147 −138 3543 −89 −8 363 3 −120 364 1 −113 365 3 −80 −56 366 3 −152 −113 367 10 −98−63 368 3 −110 −68 369 10 −101 −83 370 10 −99 −69 374 3 −119 11 375 1−126 −70 376 3 −106 −77 377 1 −151 −73 378 1 −106 −90 379 1 −118 −59 3800.3 −141 381 3 −136 382 3 −129 −74 383 3 −112 −86 334 3 −130 −93 385 10−123 −96 386 10 −83 −96 387 10 −112 −50

EFFECTS OF THE INVENTION

From the foregoing results, it is understood that the piperidinederivatives of the present invention possess hypotensive activity andare usable as hypotensives and therefore, they can be expected toprovide an excellent hypotensive effect. Accordingly, the presentinvention is extremely useful, particularly in the pharmaceuticalindustry.

Having now fully described the invention, it will be apparent to one ofordinary skill in the art that many changes and modifications can bemade thereto without departing from the spirit or scope of the inventionas set forth herein.

What is claimed as new and is intended to be secured by Letters Patentof the United States is:
 1. A piperidine compound of the formula (I)

wherein: A is pyridine; R is —H, —Cl or —OCH₃; X is —(CH₂)_(n)—,—CO—(CH₂)₃, —CONH—(CH₂)₂, —NHCO—(CH₂)₂, or —CH≡CH—(CH₂)₂—; and n is aninteger of from 3 to 5; Y is —CH≡CH—, —(CH₂)₂, —OCH₂—, —SCH₂—, or —O—;and Q is —CN, substituted or unsubstituted cyclohexyl, substituted orunsubstituted piperidinyl, substituted or unsubstituted piperazinyl,substituted or unsubstituted phenyl, substituted or unsubstituted furyl,substituted or unsubstituted thienyl, substituted or unsubstitutedpyrrolyl, substituted or unsubstituted pyridyl, substituted orunsubstituted morpholinyl, or substituted or unsubstitutedthiomorpholinyl, wherein when Q is substituted, the substituent(s)is/are selected from the group consisting of HCH₂_(n) wherein n is aninteger of 1 to 10, ClCH₂₃, allyl, phenyl, isopropyl, hydroxy,methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy,ethoxycarboxyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, cyano,imidazolylmethyl, trifluoromethyl, benzoyl, 2-hydroxybenzyl, nitro,amino, acetylamino, propanoylamino, butanoylamino, pivaloylamino,trifluoromethylamino, methoxycarbonylamino, ethoxycarbonylamino,cinnamoylamino, methanesulfonylamino, N,N-bis(methanesulfonyl)amino,aminocarbonyl, aminosulfonyl, hydroxymethyl and acetoxymethyl, andwherein when X and/or Q contain CH₂ groups, one or more of the CH₂groups in X and/or Q may be substituted by CH₂₄ CH₂₅, therebyforming a ring structure.
 2. The piperidine compound of claim 1, whereinthe hydrogen atoms of one or more of the —CH₂— groups in X and Q aresubstituted by CH₂₄ or CH₂₅, thereby forming a ring structure. 3.The piperidine compound of claim 1, wherein Q is substituted by at leastone substituent selected from the group consisting of HCH₂_(n) whereinn is an integer of 1 to 10, ClCH₂₃, allyl, phenyl, isopropyl; hydroxy,methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy,ethoxycarboxyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, cyano,imidazolylmethyl, trifluoromethyl, benzoyl, 2-hydroxybenzyl, nitro,amino, acetylamino, propanoylamino, butanoylamino, pivaloylamino,trifluoromethylamino, methoxycarbonylamino, ethoxycarbonylamino,cinnamoylamino, methanesulfonylamino, N,N-bis(methanesulfonyl)amino,aminocarbonyl, aminosulfonyl, hydroxymethyl and acetoxymethyl.
 4. Thepiperidine compound of claim 1, wherein X is —CONH—(CH₂)₂.
 5. Thepiperidine compound of claim 1, wherein Y is —CH≡CH—.
 6. The piperidinecompound of claim 1, wherein Y is —(CH₂)₂—.
 7. The piperidine compoundof claim 1, wherein Q is substituted or unsubstituted piperidinyl. 8.The piperidine compound of claim 1, wherein X is —CONH—(CH₂)₂, and Q issubstituted or unsubstituted piperidinyl.
 9. A piperidine compound ofthe formula

wherein: R is —H, —Cl or —OCH₃; X is —(CH₂)_(n)—, —CO—(CH₂)₃,—CONH—(CH₂)₂, —NHCO—(CH₂)₂, or —CH≡CH—(CH₂)₂—; and n is an integer offrom 3 to 5; Y is —CH≡CH—, —(CH₂)₂—, —OCH₂—, —SCH₂—; and Q is —CN,substituted or unsubstituted piperidinyl, substituted or unsubstitutedpiperazinyl, substituted or unsubstituted thienyl, substituted orunsubstituted morpholinyl, or substituted or unsubstitutedthiomorpholinyl, wherein when Q is substituted, the substituent(s)is/are selected from the group consisting of HCH₂_(n) wherein n is aninteger of 1 to 10, ClCH₂₃, allyl, formyl, phenyl, isopropyl, hydroxy,methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, carboxyl,methoxycarbonyl, ethoxycarbonyl, cyano, imidazolylmethyl,trifluoromethyl, benzoyl, 2-hdyroxybenzyl, nitro, amino, acetylamino,propanoylamino, butanoylamino, pivaloylamino, trifluoromethylamino,methoxycarbonylamino, ethoxycarbonylamino, cinnamoylamino,methanesulfonylamino, N,N-bis(methanesulfonyl)amino, aminocarbonyl,aminosulfonyl, hydroxymethyl and acetoxymethyl, and wherein when Xand/or Q contain CH₂groups, one or more of the CH₂ groups in Xand/or Q may be substituted by CH₂₄ or CH₂₅, thereby forming a ringstructure.
 10. The piperidine compound of claim 9, wherein X is—CONH—(CH₂)₂, Y is —CH≡CH—, and Q is N-formylpiperidinyl.
 11. Apiperidine compound of the formula

wherein: R is —H, —Cl or —OCH₃; X is —CO—(CH₂)₃, —CONH—(CH₂)₂,—NHCO—(CH₂)₂, or —CH≡CH— (CH₂)₂—; and Q is —CN, substituted orunsubstituted cyclohexyl, substituted or unsubstituted piperidinyl,substituted or unsubstituted piperazinyl, substituted or unsubstitutedphenyl, substituted or unsubstituted furyl, substituted or unsubstitutedthienyl, substituted or unsubstituted pyrrolyl, substituted orunsubstituted pyridyl, substituted or unsubstituted morpholinyl, orsubstituted or unsubstituted thiomorpholinyl, wherein when Q issubstituted, the substituent(s) is/are selected from the groupconsisting of HCH₂_(n) wherein n is an integer of 1 to 10, ClCH₂₃,allyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro,acetoxy, 2-methoxyacetoxy, ethoxycarboxyl, carboxyl, methoxycarbonyl,ethoxycarbonyl, cyano, imidazolylmethyl, trifluoromethyl, benzoyl,2-hydroxybenzyl, nitro, amino, acetylamino, propanoylamino,butanoylamino, pivaloylamino, trifluoromethylamino,methoxycarbonylamino, ethoxycarbonylamino, cinnamoylamino,methanesulfonylamino, N,N-bis(methanesulfonyl)amino, aminocarbonyl,aminosulfonyl, hydroxymethyl and acetoxymethyl, and wherein when Xand/or Q contain CH₂ groups, one or more of the CH₂ groups in Xand/or Q may be substituted by CH₂₄ or CH₂₅ thereby forming a ringstructure.
 12. A piperidine compound of the formula

wherein: R is —H, —Cl or —OCH₃; X is —(CH₂)_(n)—; n is an integer offrom 3 to 5; and Q is —CN, substituted or unsubstituted phenyl,substituted or unsubstituted furyl, substituted or unsubstitutedthienyl, substituted or unsubstituted pyrrolyl, substituted orunsubstituted pyridyl, wherein when Q is substituted, the substituent(s)is/are selected from the group consisting of HCH₂_(n) wherein n is aninteger of 1 to 10, ClCH₂₃, allyl, phenyl, isopropyl, hydroxy,methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy,ethoxycarboxyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, cyano,imidazolylmethyl, trifluoromethyl, benzoyl, 2-hydroxybenzyl, nitro,amino, acetylamino, propanoylamino, butanoylamino, pivaloylamino,trifluoromethylamino, methoxycarbonylamino, ethoxycarbonylamino,cinnamoylamino, methanesulfonylamino, N,N-bis(methanesulfonyl)amino,aminocarbonyl, aminosulfonyl, hydroxymethyl and acetoxymethyl, andwherein one or more of the CH₂ groups in X may be substituted byCH₂₄ or CH₂₅ thereby forming a ring structure.
 13. The piperidinecompounds of claim 10, wherein R is —H.